Cesium carbonate → Formate

HRID 452545

反応式

HRID 452545 の反応式
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]3[C:10]([CH2:11][NH:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1.[C:29](=O)([O-:31])[O-:30].[Cs+].[Cs+].Cl.[CH3:36][NH:37][CH2:38][CH2:39]Cl>C(#N)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:39][CH2:38][NH:37][CH3:36])[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1.[CH:29]([O-:31])=[O:30]

参加物

6

反応物 3

HCID 10796Cesium carbonate2 回HCID 3028223Ethanamine, 2-chloro-N-methyl-, hydrochloride (1:1)2 回HCID 178505857HCID 178505857、化合物

生成物 2

HCID 283FormateHCID 178484193HCID 178484193、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

A mixture of trans-8-chloro-1-[4-(3-fluoro-pyridin-2-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (50.0 mg, 0.126 mmol), cesium carbonate (246 mg, 0.754 mmol) and 2-methylaminoethyl chloride hydrochloride (65.4 mg, 0.503 mmol) in acetonitrile (1.3 ml) was heated at 70° C. for 20 h. After addition of further portions of cesium carbonate (246 mg, 0.754 mmol) and 2-methylaminoethyl chloride hydrochloride (65.4 mg, 0.503 mmol) the mixture was heated at 70° C. for another 20 h. The reaction mixture was partitioned between 1 M aqueous sodium hydroxide solution (2 ml) and ethyl acetate (5 ml). The layers were separated. The aqueous layer was extracted with two 5-ml portions of ethyl acetate. The combined organic layers were concentrated in vacuo. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave the title compound as formate salt. The salt was partitioned between ethyl acetate (15 ml) and 1 M aqueous sodium hydroxide solution (10 ml). The layers were separated. The aqueous layer was extracted with two 15 ml-portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (14 mg, 25%) as off-white solid. MS m/e: 455 ([M+H]+)

後処理

  1. temperaturewas heated at 70° C. for another 20 h
  2. customThe reaction mixture was partitioned between 1 M aqueous sodium hydroxide solution (2 ml) and ethyl acetate (5 ml)
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted with two 5-ml portions of ethyl acetate
  5. concentrationThe combined organic layers were concentrated in vacuo

出典と根拠

ORDレコード
ord-2e4e64ee572a4846a88819af73d74256
出典データセット
uspto-grants-2013_07
特許番号
US08492376B2

関連ノート

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